JP2019524705A5 - - Google Patents
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- Publication number
- JP2019524705A5 JP2019524705A5 JP2019500377A JP2019500377A JP2019524705A5 JP 2019524705 A5 JP2019524705 A5 JP 2019524705A5 JP 2019500377 A JP2019500377 A JP 2019500377A JP 2019500377 A JP2019500377 A JP 2019500377A JP 2019524705 A5 JP2019524705 A5 JP 2019524705A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- benzyl
- chloro
- methoxy
- oxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 229910052739 hydrogen Inorganic materials 0.000 claims 28
- 239000001257 hydrogen Substances 0.000 claims 28
- 125000005843 halogen group Chemical group 0.000 claims 26
- 150000002431 hydrogen Chemical class 0.000 claims 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 20
- -1 -N (CH 3) 2 Chemical group 0.000 claims 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 7
- 125000003368 amide group Chemical group 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000004429 atom Chemical group 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 239000011593 sulfur Substances 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000002619 bicyclic group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- GXZGAKZGEMMYNJ-JGCGQSQUSA-N (2R)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-(4-formyl-3,5-dimethylpyrazol-1-yl)-2-methylphenyl]methoxy]phenyl]methylamino]-3-hydroxy-2-methylpropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@@](C(=O)O)(CO)C)C=1)OCC=1C=NC=C(C=1)C#N)OCC1=C(C(=CC=C1)N1N=C(C(=C1C)C=O)C)C GXZGAKZGEMMYNJ-JGCGQSQUSA-N 0.000 claims 1
- NUSXRHUFHUAGCW-NXVGIJDASA-N (2R)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[1-[4-[(3S)-3-hydroxypyrrolidin-1-yl]butyl]-3,5-dimethylpyrazol-4-yl]-2-methylphenyl]methoxy]phenyl]methylamino]-3-hydroxy-2-methylpropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@@](C(=O)O)(CO)C)C=1)OCC=1C=NC=C(C=1)C#N)OCC1=C(C(=CC=C1)C=1C(=NN(C=1C)CCCCN1C[C@H](CC1)O)C)C NUSXRHUFHUAGCW-NXVGIJDASA-N 0.000 claims 1
- MWUOFFRBBLJGJC-JQMWFGOGSA-N (2R)-2-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[4-[[(3R)-3-hydroxypyrrolidin-1-yl]methyl]-3,5-dimethylpyrazol-1-yl]-2-methylphenyl]methoxy]phenyl]methylamino]-3-hydroxy-2-methylpropanoic acid Chemical compound ClC=1C(=CC(=C(CN[C@@](C(=O)O)(CO)C)C=1)OCC=1C=NC=C(C=1)C#N)OCC1=C(C(=CC=C1)N1N=C(C(=C1C)CN1C[C@@H](CC1)O)C)C MWUOFFRBBLJGJC-JQMWFGOGSA-N 0.000 claims 1
- ZXGHTQAKECUTMN-KUFVUHJUSA-N (2S)-1-[[5-chloro-2-[(5-cyanopyridin-3-yl)methoxy]-4-[[3-[1-[3-[(3R)-3-hydroxypyrrolidin-1-yl]propyl]-2-oxopyridin-3-yl]-2-methylphenyl]methoxy]phenyl]methyl]piperidine-2-carboxylic acid Chemical compound ClC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=1)OCC=1C=NC=C(C=1)C#N)OCC1=C(C(=CC=C1)C=1C(N(C=CC=1)CCCN1C[C@@H](CC1)O)=O)C ZXGHTQAKECUTMN-KUFVUHJUSA-N 0.000 claims 1
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- SWJOCPYUANLJCB-UUWRZZSWSA-N BrC1=CC=C2N=CC(=NC2=C1)C=1C(=C(COC2=CC(=C(CN[C@@](C(=O)O)(CO)C)C=C2Cl)OCC=2C=NC=C(C=2)C#N)C=CC=1)C Chemical compound BrC1=CC=C2N=CC(=NC2=C1)C=1C(=C(COC2=CC(=C(CN[C@@](C(=O)O)(CO)C)C=C2Cl)OCC=2C=NC=C(C=2)C#N)C=CC=1)C SWJOCPYUANLJCB-UUWRZZSWSA-N 0.000 claims 1
- FFDMQWOCFFLAMR-UHFFFAOYSA-N ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC1=C(C(=CC=C1)C1=C(C(=NC=C1)OCCCN1CCCCC1)Cl)C)CNC(CO)(CO)C Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC1=C(C(=CC=C1)C1=C(C(=NC=C1)OCCCN1CCCCC1)Cl)C)CNC(CO)(CO)C FFDMQWOCFFLAMR-UHFFFAOYSA-N 0.000 claims 1
- PIFUSVHHVLNCQH-MUUNZHRXSA-N ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC1=C(C(=CC=C1)C1=NC(=CC=C1)OCCCN1C[C@@H](CC1)O)C)CO Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC1=C(C(=CC=C1)C1=NC(=CC=C1)OCCCN1C[C@@H](CC1)O)C)CO PIFUSVHHVLNCQH-MUUNZHRXSA-N 0.000 claims 1
- POPXQHLYZQCOTH-UHFFFAOYSA-N ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC1=C(C(=CC=C1)C1=NC=CC(=C1Cl)OCCCO)C)CNC(CO)(CO)C Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC1=C(C(=CC=C1)C1=NC=CC(=C1Cl)OCCCO)C)CNC(CO)(CO)C POPXQHLYZQCOTH-UHFFFAOYSA-N 0.000 claims 1
- UVRIYWVLPXFKJP-MUUNZHRXSA-N ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC1=C(C(=CC=C1)C=1C=CC2=C(N=C(O2)CCN2C[C@@H](CC2)O)C=1)C)C=O Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC1=C(C(=CC=C1)C=1C=CC2=C(N=C(O2)CCN2C[C@@H](CC2)O)C=1)C)C=O UVRIYWVLPXFKJP-MUUNZHRXSA-N 0.000 claims 1
- PHOFLIDUQMGIEX-FIRIVFDPSA-N ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC1=C(C(=CC=C1)N1N=C(C(=C1C)CN1C[C@@H](CC1)O)C)C)CN1C[C@@H](CC1)O Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC1=C(C(=CC=C1)N1N=C(C(=C1C)CN1C[C@@H](CC1)O)C)C)CN1C[C@@H](CC1)O PHOFLIDUQMGIEX-FIRIVFDPSA-N 0.000 claims 1
- IDLUKFOTOBOHGX-UHFFFAOYSA-N ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC1=NC=CC(=C1C)C1=C(C(=CC=C1)OCCCN1CCCCC1)C)CNC(CO)(CC)CO Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC1=NC=CC(=C1C)C1=C(C(=CC=C1)OCCCN1CCCCC1)C)CNC(CO)(CC)CO IDLUKFOTOBOHGX-UHFFFAOYSA-N 0.000 claims 1
- AKKBIEZYVLKDMU-JGCGQSQUSA-N ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC1=NC=CC(=C1C)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)CNC(CO)(CC)CO Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC1=NC=CC(=C1C)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)CNC(CO)(CC)CO AKKBIEZYVLKDMU-JGCGQSQUSA-N 0.000 claims 1
- NKGHXZANVYAHOW-JGCGQSQUSA-N ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC=1C=NC=C(C=1C)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)CNC(CO)(CO)C Chemical compound ClC1=CC(=C(OCC=2C=NC=C(C#N)C=2)C=C1OCC=1C=NC=C(C=1C)C1=C(C(=CC=C1)OCCCN1C[C@@H](CC1)O)C)CNC(CO)(CO)C NKGHXZANVYAHOW-JGCGQSQUSA-N 0.000 claims 1
- AGPGILJKTUMUJW-KUFVUHJUSA-N ClC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=1)OCC=1C=NC=C(C=1)C#N)OCC1=C(C(=CC=C1)C1=NC(=CC=C1)OCCCN1C[C@@H](CC1)O)C Chemical compound ClC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=1)OCC=1C=NC=C(C=1)C#N)OCC1=C(C(=CC=C1)C1=NC(=CC=C1)OCCCN1C[C@@H](CC1)O)C AGPGILJKTUMUJW-KUFVUHJUSA-N 0.000 claims 1
- STDOIPYSVOFITM-XIFFEERXSA-N ClC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=1)OCC=1C=NC=C(C=1)C#N)OCC1=C(C(=CC=C1)C=1C=C2N=CC=NC2=CC=1)C Chemical compound ClC=1C(=CC(=C(CN2[C@@H](CCCC2)C(=O)O)C=1)OCC=1C=NC=C(C=1)C#N)OCC1=C(C(=CC=C1)C=1C=C2N=CC=NC2=CC=1)C STDOIPYSVOFITM-XIFFEERXSA-N 0.000 claims 1
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- 2017-07-05 EA EA201990221A patent/EA201990221A1/ru unknown
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- 2017-07-05 KR KR1020197003664A patent/KR102491992B1/ko active Active
- 2017-07-05 WO PCT/US2017/040663 patent/WO2018009505A1/en not_active Ceased
- 2017-07-05 EP EP17740229.4A patent/EP3481815B1/en active Active
- 2017-07-05 US US16/315,800 patent/US10590105B2/en active Active
- 2017-07-05 AU AU2017292758A patent/AU2017292758A1/en not_active Abandoned
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- 2017-07-05 CN CN201780054779.7A patent/CN109689640B/zh active Active
- 2017-07-05 JP JP2019500377A patent/JP7168551B2/ja active Active
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